Reaction #78795

ord-9d2b141ac7a345f3a67ae2d06bc2c97c

Reaction equation

Nc1cccc(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)c1
3-(perfluoro-n-octyl)benzenamine
O=[N+]([O-])c1ccc(F)c([N+](=O)[O-])c1
2,4-dinitrofluorobenzene
CN1CCCC1=O
NMP
→
O=[N+]([O-])c1ccc(Nc2cccc(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)c2)c([N+](=O)[O-])c1
N-[3-(perfluorooctyl)phenyl]-2,4-dinitrobenzenamine
Yield 83.2%

Reactants

Nc1cccc(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)c1
3-(perfluoro-n-octyl)benzenamine
O=[N+]([O-])c1ccc(F)c([N+](=O)[O-])c1
2,4-dinitrofluorobenzene
CN1CCCC1=O
NMP

Reagents

None

Solvents

CCN(CC)CC
triethylamine

Conditions

Temperature
70°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ExtractionExtraction and recrystallization from hexane-ethyl acetate

Procedure

A mixture of 3-(perfluoro-n-octyl)benzenamine (2.04 g), 2,4-dinitrofluorobenzene (0.78 g), NMP (8 mL) and triethylamine (0.85 mL) was heated to 70° C. for 16 hr. Extraction and recrystallization from hexane-ethyl acetate gave N-[3-(perfluorooctyl)phenyl]-2,4-dinitrobenzenamine (2.25 g, mp 124.5-125° C.).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06713135B2uspto-grants-2004_03